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1121-66-0

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1121-66-0 Usage

Uses

A cycloheptenone derivative, a key intermediate for the synthesis of perhydroazulene terpenoids.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 2073, 1976 DOI: 10.1021/jo00873a055

General Description

2-Cyclohepten-1-one is an α,β-enone and its regioselective reaction with allyl indium reagent in the presence of TMSCl has been reported. It reacts with Bu2Zn in the presence of catalytic amounts of Cu(OTf)2 and CH2-bridged azolium salts to give (S)-3-butylcycloheptanone.

Check Digit Verification of cas no

The CAS Registry Mumber 1121-66-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 1 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1121-66:
(6*1)+(5*1)+(4*2)+(3*1)+(2*6)+(1*6)=40
40 % 10 = 0
So 1121-66-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O/c8-7-5-3-1-2-4-6-7/h3,5H,1-2,4,6H2

1121-66-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Cycloheptenone

1.2 Other means of identification

Product number -
Other names Cyclohept-2-enone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1121-66-0 SDS

1121-66-0Relevant articles and documents

Medium-Ring Systems. 5. Synthesis and Base-Catalyzed Isomerizations of Medium-Ring Cycloalkenones with Electron-Withdrawing Substituents

Mease, Ronnie C.,Hirsch, Jerry A.

, p. 2925 - 2937 (1984)

Medium-ring 3-cycloalkenones with electron-withdrawing substituents at the 3-position have been synthesized and subjected to base-catalyzed isomerizations.In a given ring size in the seven- and eight-membered carbocycles, the substituents studied caused similar shifts in the equilibria toward the 3-cycloalkenones relative to the unsubstituted cases.Steric effects of the substituents are therefore not significant.As the ring size is increased, the preference for the 3-cycloalkenone becomes more pronounced.In the nine- and ten-membered systems, an additional equilibrium involving formation of 4-cycloalkenones appears.Decreased effectiveness of conjugative interactions in endocyclic dienolates and in 2-cycloalkenones with increasing ring size is suggested.

ENONE SYNTHESIS VIA α-PYRIDYLSELENO CARBONYL COMPOUNDS

Toshimitsu, Akio,Owada, Hiroto,Uemura, Sakae,Okano, Masaya

, p. 2105 - 2108 (1982)

Oxidative elimination of α-pyridylseleno carbonyl compounds affords enones in excellent yields, providing an improved method for dehydrogenation of ketones and aldehydes.These results indicate that pyridylseleno group is a better leaving group than phenylseleno group in selenoxide elimination leading to enones.

Allylic oxidation of olefins with a manganese-based metal-organic framework

Chen, Jingwen,Chen, Minda,Zhang, Biying,Nie, Renfeng,Huang, Ao,Goh, Tian Wei,Volkov, Alexander,Zhang, Zhiguo,Ren, Qilong,Huang, Wenyu

, p. 3629 - 3636 (2019)

Selective oxidation of olefins to α,β-unsaturated ketones under mild reaction conditions has attracted considerable interest, since α,β-unsaturated ketones can serve as synthetic precursors for various downstream chemical products. The major inherent challenges with this chemical oxidation are chemo- and regio-selectivity as well as environmental concerns, i.e. catalyst recycle, safety and cost. Using atmospheric oxygen as an environmentally friendly oxidant, we found that a metal-organic framework (MOF) constructed with Mn and a tetrazolate ligand (CPF-5) showed good activity and selectivity for the allylic oxidation of olefins to α,β-unsaturated ketones. Under the optimized conditions, we could achieve 98% conversion of cyclohexene and 87% selectivity toward cyclohexanone. The combination of a substoichiometric amount of TBHP (tert-butylhydroperoxide) and oxygen not only provides a cost effective oxidation system but significantly enhances the selectivity to α,β-unsaturated ketones, outperforming most reported oxidation methods. This catalytic system is heterogeneous in nature, and CPF-5 could be reused at least five times without a significant decrease in its catalytic activity and selectivity.

Enzymatic allylic oxidations with a lyophilisate of the edible fungus Pleurotus sapidus

Rickert, Aljona,Krombach, Verena,Hamers, Oliver,Zorn, Holger,Maison, Wolfgang

, p. 639 - 644 (2012)

Allylic oxidations belong to the most attractive synthetic transformations because they convert readily available and cheap starting materials into value-added products. In this study, we describe oxidative conversions of terpenoids and a number of related cycloalkenes with a lyophilisate of the edible fungus Pleurotus sapidus. The biocatalytic protocol is simple and the biocatalyst is readily available. The conversions of various cycloalkenes proceed cleanly in most cases to the corresponding enones. The substrate scope is remarkable and includes a number of mono- and sequiterpenes, functionalized terpenoids as well as simple cyclohexenes and benzylic substrates. Enzymatic allylic oxidations by Pleurotus sapidus are thus an excellent non-toxic alternative to metal-mediated oxidation procedures in academic labs and for industrial application in food technology, cosmetics or pharmaceutical research. The Royal Society of Chemistry 2012.

PINO/NHPI-mediated selective oxidation of cycloalkenes to cycloalkenones: Via a photo-electrochemical method

Tateno, Hiroyuki,Miseki, Yugo,Sayama, Kazuhiro

, p. 9339 - 9342 (2019)

The selective photo-electrochemical oxidation of cyclohexene to 2-cyclohexene-1-one was successfully performed with excellent Faraday efficiency (>99%) via indirect oxidation with a PINO/NHPI mediator and O2 on a BiVO4/WO3 photoanode under low applied bias.

Facile ring opening of tertiary aminocyclopropanes by photooxidation

Lee,U,Blackstock,Cha

, p. 10241 - 10242 (1997)

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Olah,G.A.,Liang,G.

, p. 6434 - 6441 (1972)

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IBX in an ionic liquid: Eco-friendly oxidation of 17α- methylandrostan-3β,17β-diol, an intermediate in the synthesis of anabolic oxandrolone

Chhikara, Bhupender S.,Chandra, Ramesh,Tandon, Vibha

, p. 7585 - 7588 (2004)

An easily available hypervalent iodine(V) reagent, 2-iodoxybenzoic acid (IBX) immobilized in the ionic liquid [bmim][Br] was found to be an efficient and eco-friendly protocol for the oxidation of 17α-methylandrostan- 3β,17β-diol (1). At ambient temperature oxidation of 1 with IBX gave mestanolone (2) in good yield and with an increased stoichiometric amount of IBX, oxidation adjacent to the carbonyl functionality (α,β- unsaturation) occurred to give dehydrogenated 17β-hydroxy-17α-methyl- Δ1-androsten-3-one (3) as the major product in a one-pot reaction. The product is easily obtained by extraction with diethyl ether and evaporation of the solvent.

Eaton,Lin

, p. 2052,2053 (1965)

N-Hydroxyphthalimide Anchored on Diamond Nanoparticles as a Selective Heterogeneous Metal-free Oxidation Catalyst of Benzylic Hydrocarbons and Cyclic Alkenes by Molecular O2

Blandez, Juan F.,Navalón, Sergio,álvaro, Mercedes,García, Hermenegildo

, p. 198 - 205 (2018)

N-hydroxyphthalimide (NHPI) derived from trimellitic anhydride has been covalently anchored (4 wt %) through ester bonds to the surface of commercial diamond nanoparticles previously functionalized by chemical and thermal treatments (DH). IR spectroscopy of the NHPI/DH solid shows the presence of a characteristic peak at 1735 cm?1 attributable to the ester bond, while solid-state MAS 13C NMR spectroscopy shows two broad bands corresponding to carbon atoms of carbonyl groups (167 ppm) and aromatic carbons (127 ppm). NHPI/DH promotes autoxidation of isobutylbenzene involving superoxide (O2 .?) and hydroperoxide (HOO?) radicals; NHPI/DH can be reused at least three times and reach a minimum turnover number as high as 20 600, which is probably due to the inertness of the diamond surface, allowing free diffusion of reactive oxygen species. Analogous materials in which NHPI was anchored on activated carbon and multiwall carbon nanotubes were inefficient as autoxidation catalysts. NHPI/DH is able to promote also selective aerobic oxidation of other benzylic hydrocarbons and cycloalkenes.

g-C3N4/metal halide perovskite composites as photocatalysts for singlet oxygen generation processes for the preparation of various oxidized synthons

Corti, Marco,Chiara, Rossella,Romani, Lidia,Mannucci, Barbara,Malavasi, Lorenzo,Quadrelli, Paolo

, p. 2292 - 2298 (2021/04/12)

g-C3N4/metal halide perovskite composites were prepared and used for the first time as photocatalysts forin situ1O2generation to perform hetero Diels-Alder, ene and oxidation reactions with suitable dienes and alkenes. The standardized methodology was made applicable to a variety of olefinic substrates. The scope of the method is finely illustrated and the reactions afforded desymmetrized hydroxy-ketone derivatives, unsaturated ketones and epoxides. Some limitations were also observed, especially in the case of the alkene oxidations, and poor chemoselectivity was somewhere observed in this work which is the first application of MHP-based composites forin situ1O2generation. The experimental protocol can be used as a platform to further expand the knowledge and applicability of MHPs to organic reactions, since perovskites offer a rich variety of tuning strategies which may be explored to improve reaction yields and selectivities.

Aerobic oxidation of the C-H bond under ambient conditions using highly dispersed Co over highly porous N-doped carbon

Nie, Renfeng,Chen, Jingwen,Chen, Minda,Qi, Zhiyuan,Goh, Tian-Wei,Ma, Tao,Zhou, Lin,Pei, Yuchen,Huang, Wenyu

, p. 1461 - 1466 (2019/03/26)

Highly dispersed Co sites in highly porous N-doped carbon (Co-NC) were synthesized by high-temperature pyrolysis of Zn/Co bimetallic zeolitic imidazolate framework-8 (CoxZn100-x-ZIF). Wide characterization indicated that the pyrolysis atmosphere and temperature play crucial roles in the metal dispersion and pore structure of the resulting materials. A hydrogen treatment at elevated temperatures is found to favour the Zn volatilization and restrict the pore shrinkage of the ZIF precursor, thus yielding efficient catalysts with highly dispersed Co, a high surface area (1090 m2 g-1) and pore volume (0.89 cm3 g-1). When used as a catalyst for aerobic oxidation of ethylbenzene (EB), Co1Zn99-ZIF-800-H2 contributes to 98.9% EB conversion and 93.1% ketone selectivity under mild conditions (60 °C, 1 atm O2), which is 41.3 times more active in comparison to the ZIF-67-derived Co catalyst. Co-NC is stable and could be reused four times without obvious deactivation. This catalyst displays good chemoselectivity to the corresponding ketones when using a broad scope of hydrocarbon compounds.

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